The Aviator
Leo nailed his role as eccentric billionaire, Howard Hughes in the film The Aviator. While Leo still looked very young, his acting skills helped him take charge of the difficult role of the real life story of the famed aviator.
Blooper: In one scene in the movie, Leonardo DiCaprio buys a package of chocolate chip cookies. Unfortunately, the writers must have overlooked the fact that these cookies weren’t created until 1930, two years after the the date in which the movie takes place.